Wondering why the record keeping is such a chore. Ever hear of Quicken?

I stick all medical and charitable receipts into their respective manila folders inside a tax file for each year and periodically arrange them in chronological order. I keep track of our expenditures on a monthly basis. At the end of each month I go over the credit card bills and bank statement and enter all medical and charitable expenditures into an Excel spreadsheet. At the end of the year I match the spreadsheet against the receipts. Nothing as sophisticated as Quicken is needed. It takes me probably no more than an hour per year total to come up with our medical and charitable deductions for Schedule A--90 minutes tops.

More to the point, using Quicken does not eliminate the need to have receipts proving charitable and medical expenses. Further, user error in Quicken can produce the wrong answer for taxes. If I put $5 in the Salvation Army kettle, that's charity in Quicken. But I have no receipt, so it's not charity on my Schedule A.

It's actually easier for me to track this stuff with a paper file and an Excel spreadsheet than to extract it from Quicken and be sure the answer Quicken gives me is supportable.